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Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Winter Garden cottages

House (2 Bedrooms) | Interior

Fire Pit & Yard: Updated Winter Garden Home!

Fire Pit & Yard: Updated Winter Garden Home!
3.0 star property
Winter Garden
The price is €434
includes taxes & fees
2 May - 3 May
Fire Pit & Yard: Updated Winter Garden Home!
Exterior

“Best Stay Ever” – Recent Guest

“Best Stay Ever” – Recent Guest
Lake Mary
9.8 out of 10, Exceptional, (51 reviews)
"Everything was wonderful! We loved the location and the house was cozy and comfortable. "
United States
Mike B.
The price is €220
includes taxes & fees
27 May - 28 May
“Best Stay Ever” – Recent Guest
Terrace/patio

Relax Tonight. Cozy, Quiet and Super Clean.

Relax Tonight. Cozy, Quiet and Super Clean.
Lake Mary
10.0 out of 10, Exceptional, (19 reviews)
"Easy access, perfect location, perfectly appointed. Will stay again :-)"
United States
Tricia S.
The price is €217
includes taxes & fees
11 May - 12 May
Relax Tonight. Cozy, Quiet and Super Clean.
Property grounds

Tiny Hidden Cottage

Tiny Hidden Cottage
Longwood
9.4 out of 10, Exceptional, (66 reviews)
"Great place, found the heater, thank you!Would stay again, just pull the bed away from the wall for us old folk "
United States
Susan J.
The price is €127
includes taxes & fees
27 Apr - 28 Apr
Tiny Hidden Cottage
Interior

Downtown Cottage

Downtown Cottage
Colonialtown North
8.2 out of 10, Very good, (11 reviews)
"Clean perfect location for what we needed "
United States
Jerred B.
The price is €175
includes taxes & fees
11 May - 12 May
Downtown Cottage
Exterior

Incredible Private Lakefront Cottage Retreat

Incredible Private Lakefront Cottage Retreat
Altamonte Springs
10.0 out of 10, Exceptional, (34 reviews)
"The host was easy to contact and the cottage was very cozy with all necessary amenities. The lakeside location was both beautiful and peaceful, especially considering it is so close to 436 and I4. We definitely plan to return. "
United States
Carol G.
The price is €290
includes taxes & fees
29 Apr - 30 Apr
Incredible Private Lakefront Cottage Retreat
Exterior

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!

The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
College Park
9.8 out of 10, Exceptional, (37 reviews)
"Lovely spot, in a quiet neighborhood. Clean and spotless, and stocked with amenities for breakfast and snacks. We'll be booking again next time we go down to visit family in Orlando."
United States
John
The price is €281
includes taxes & fees
27 Apr - 28 Apr
The Coach House- Entire Home - 2 bedroom/3 bath Orlando getaway!
House (5 Bedrooms) | Interior

Upstay - Resort Home w Cinema, Pool & Lake View

Upstay - Resort Home w Cinema, Pool & Lake View
3.0 star property
Kissimmee
The price is €386
includes taxes & fees
30 Apr - 1 May
Upstay - Resort Home w Cinema, Pool & Lake View
Exterior

Perfect Place for a Perfect Vacation

Perfect Place for a Perfect Vacation
Kissimmee
10.0 out of 10, Exceptional, (1 review)
The price is €167
includes taxes & fees
27 Apr - 28 Apr
Perfect Place for a Perfect Vacation
Exterior

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee

Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Kissimmee
10.0 out of 10, Exceptional, (2 reviews)
"We stayed and visited universal snd drove to Jacksonville it was a cute cottage"
United States
Jennifer b.
The price is €250
includes taxes & fees
27 Apr - 28 Apr
Beautiful Cottage! Your Home Away From Home. 4 miles from Disney, Kissimmee
Microwave, stovetop

Tiny house close to Disney KISSIMMEE

Tiny house close to Disney KISSIMMEE
Kissimmee
8.4 out of 10, Very good, (6 reviews)
"Just needed a place to stay close to Disney for the night and the place was clean and easy to check in and out. "
United States
Jena B.
The price is €152
includes taxes & fees
11 May - 12 May
Tiny house close to Disney KISSIMMEE
Smart TV, books

Family-Friendly Cottage Near Orlando’s Top Attractions

Family-Friendly Cottage Near Orlando’s Top Attractions
Kissimmee
10.0 out of 10, Exceptional, (1 review)
"Perfect location to enjoy Universal Epic and Islands of Adventure with only a 15 minute ride. The beds were very comfortable and the place is clean. We were welcomed with a cute sign, bottled water and cookies. Will definitely stay here again!"
United States
Joyce R.
The price is €178
includes taxes & fees
6 May - 7 May
Family-Friendly Cottage Near Orlando’s Top Attractions
Dining

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC

Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Kissimmee
The price is €190
includes taxes & fees
30 Apr - 1 May
Mickey's Hideaway Cottage 4 miles from Disney in Kissimmee with WiFi and AC
Exterior

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD

MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
Davenport
5.0 out of 10, (2 reviews)
"Needs some upgrades. The bed was a full size, very small for a couple, should really think of upgrading to a king. Pans were old and could use replacing. Bugs and ants constant. Shower was small. Very small tv. Stovetop had missing nob and was difficult to operate. Definitely needs upgrading, left a day early, didn’t feel comfortable there. "
United States
Rebecca F.
The price is €137
includes taxes & fees
4 May - 5 May
MID CENTURY TINY FOREST HOME CLOSE TO DISNEY WORLD
House (4 Bedrooms) | Interior

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool

~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
3.0 star property
Indian Ridge
The price is €402
includes taxes & fees
9 May - 10 May
~ 5 Mi to Theme Parks: Kissimmee Home w/ Pool
The Garden, Pet Friendly | Terrace/patio

Historic Tremain Cottages

Historic Tremain Cottages
3.0 star property
Mount Dora
8.6 out of 10, Excellent, (37 reviews)
"Very clean room, quaint, close to the downtown area. "
United States
Raymond
The price is €155
includes taxes & fees
27 Apr - 28 Apr
Historic Tremain Cottages
House (3 Bedrooms) | Living area

Serenity - Family & Pet Friendly, Amazing Location

Serenity - Family & Pet Friendly, Amazing Location
3.0 star property
Crestwynd Bay
The price is €340
includes taxes & fees
27 Apr - 28 Apr
Serenity - Family & Pet Friendly, Amazing Location
House (3 Bedrooms) | Interior

Upstay: Bright Family-friendly Retreat With Patio

Upstay: Bright Family-friendly Retreat With Patio
3.0 star property
Chatham Park
The price is €230
includes taxes & fees
28 Apr - 29 Apr
Upstay: Bright Family-friendly Retreat With Patio
Exterior

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas

Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
3.5 star property
Reunion
The price is €564
includes taxes & fees
13 May - 14 May
Refurbished Lux 6 Bed Golf Views at Reunion Resort by Shine Villas
Exterior

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney

"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Kissimmee
9.6 out of 10, Exceptional, (9 reviews)
"Great place for a stay, clean and plenty of everything you need. "
United States
Leo C.
The price is €265
includes taxes & fees
25 May - 26 May
"Casa Kiwi" Margaritaville Cottage 5 minutes to Disney
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Winter Garden Hotel Reviews

The Grove Resort & Water Park Orlando

The Grove Resort & Water Park Orlando

8/10 Good
"Properties not too bad had we ended up changing rooms because the front of the hotel was very noisy. They were able to accommodate us because it wasn’t so busy. The hotel has definitely been heavily used although the stay was still nice. Everything in the hotel is very expensive. Food quality isn’t the greatest for the prices."
SALVATORE 10-night trip
Posted 1 hour ago
The Grove Resort & Water Park Orlando

Find out more about Winter Garden

Winter Garden Cottages information

Number of reviews
264
Accommodation
2480 Cottages
Lowest Price
€127
Highest Price
€564

Frequently asked questions

How much do cottages in Winter Garden cost?
Cottages in Winter Garden range between €127 and €564 per night. These stays offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Winter Garden with Expedia?
Expedia has some great cottages in Winter Garden, so get ready for a memorable holiday on nature's doorstep. If you're sticking to a budget, select how much you'd like to spend and the preferred star rating of your property. Or, use our filters to search for cottages with free WiFi or a kitchen. We'll help you find the right fit whatever your bank balance or plans.
How can I find cheap cottages in Winter Garden?
With Expedia's convenient filter tool, scoring cheap cottages in Winter Garden has never been simpler. To discover accommodation that'll make your wallet happy, fine-tune your search results by budget, star rating and amenities.
What is there to do in Winter Garden near my cottage?
Whatever you're into, Winter Garden has plenty of things to keep you on the go. Orange County National Golf Club, Resurrection Catholic Church and West Orange Trail are on many travellers' agendas. Don't forget to explore Winter Garden Art Association, Winter Garden Heritage Museum and Oakland Nature Preserve either. With Expedia's Winter Garden hotel deals, you'll be able to see more renowned attractions like these with the cash you save.